Gold-catalyzed regiospecific C-H annulation of o-ethynylbiaryls with anthranils: π-extension by ring-expansion en route to N-doped PAHs
We describe a novel, short, and flexible approach to diverse N-doped polycyclic aromatic hydrocarbons (PAHs) through gold-catalyzed π-extension of anthranils with o-ethynylbiaryls as reagents. This strategy uses easily accessible starting materials, is simple due to high step and atom economy, and s...
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| Main Authors: | , , , , , |
|---|---|
| Format: | Article (Journal) |
| Language: | English |
| Published: |
06 April, 2018
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| In: |
Angewandte Chemie. International edition
Year: 2018, Volume: 57, Issue: 23, Pages: 6935-6939 |
| ISSN: | 1521-3773 |
| DOI: | 10.1002/anie.201802445 |
| Online Access: | Verlag, Volltext: http://dx.doi.org/10.1002/anie.201802445 Verlag, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201802445 
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| Author Notes: | Zhongyi Zeng, Hongming Jin, Kohei Sekine, Matthias Rudolph, Frank Rominger, A. Stephen K. Hashmi |
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| 245 | 1 | 0 | |a Gold-catalyzed regiospecific C-H annulation of o-ethynylbiaryls with anthranils |b π-extension by ring-expansion en route to N-doped PAHs |c Zhongyi Zeng, Hongming Jin, Kohei Sekine, Matthias Rudolph, Frank Rominger, A. Stephen K. Hashmi |
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| 520 | |a We describe a novel, short, and flexible approach to diverse N-doped polycyclic aromatic hydrocarbons (PAHs) through gold-catalyzed π-extension of anthranils with o-ethynylbiaryls as reagents. This strategy uses easily accessible starting materials, is simple due to high step and atom economy, and shows good functional-group compatibility as well as scale-up potential. Mechanistically, the tandem reaction is proposed to involve a nucleophilic addition/ring opening/regiospecific C−H annulation/protodeauration sequence terminated by a Friedel-Crafts-type cyclization. Photophysical studies of the products indicated violet-blue fluorescence emission with quantum yields up to 0.45. | ||
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